Synthesis and 13C nuclear magnetic resonance assignments of cannithrene 1: a cannabis constituent

Author:

El-Feraly Farouk S.,Cheatham Steve F.,McChesney James D.

Abstract

Two synthetic approaches to cannithrene 1 (1) have been explored. One-pot annelation of 6,8-dimethoxytetralone by first forming a β-keto sulfoxide, then addition of methyl vinyl ketone, gave, unexpectedly, after elimination of the sulfoxide, the naphthol (10). The successful route to cannithrene 1 (1) involved regiospecific demethylation of 6,8-dimethoxytetralone, then its conversion to enone 16. Pyridinium bromide perbromide provided the necessary aromatization to give cannithrene 1 (1) after deprotection by hydrogenolysis. The 13C nmr assignments of 1 were made.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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